Water → HCID 19788165, compound

HRID 1656479Notes

Reaction equation

HRID 1656479 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11]Br)[CH:5]=1.[C:14]([O-:17])(=[O:16])[CH3:15].[K+].O>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH2:11][O:17][C:14](=[O:16])[CH3:15])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 517044Potassium AcetateHCID 19349393Methyl 3-(Bromomethyl)-5-methylbenzoate

Product 1

HCID 19788165HCID 19788165, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 5 liter flask were combined 507 g (2.09 mole) of methyl-3-bromomethyl-5-methylbenzoate with 615 g (6.3 mole) of potassium acetate in 2850 ml of glacial acetic acid and refluxed for 3 hours. The contents of the flask were then cooled down to room temperature and divided in 3 equal portions for work up. Each portion was poured into 2 liter of water and extracted with ethyl ether (3×300 ml). The combined organic layers were washed with water (3×600 ml) and then with 2% aqueous sodium hydroxide (5×200 ml) and then dried over sodium sulfate. The solvent was then eliminated in the rotavap to give 420.8 g (90% yield) of crude product, used as such in the next step.

Workup

  1. customIn a 5 liter flask were combined
  2. extractionextracted with ethyl ether (3×300 ml)
  3. washThe combined organic layers were washed with water (3×600 ml)
  4. dry with materialwith 2% aqueous sodium hydroxide (5×200 ml) and then dried over sodium sulfate

Sources & evidence

ORD record
ord-6b2c8900353141b4a50aec1bbafad86b
Source dataset
uspto-grants-1993_10
Patent number
US05254584

Reaction notes

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